1-Hydroxybenzotriazole → N-[[5-amino-4-[(3,4-difluorophenyl)hydrazinylidene]pyrazol-3-yl]methyl]-2-chloro-6-methylpyridine-3-carboxamide

HRID 255010Notes

Reaction equation

HRID 255010 reaction equation
N=C=N.C1C=CC2N(O)N=NC=2C=1.[Cl:14][C:15]1[N:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=O.[NH2:25][CH2:26][C:27]1[C:28](=[N:33][NH:34][C:35]2[CH:40]=[CH:39][C:38]([F:41])=[C:37]([F:42])[CH:36]=2)[C:29]([NH2:32])=[N:30][N:31]=1>C(Cl)Cl.CN(C=O)C>[NH2:32][C:29]1[C:28](=[N:33][NH:34][C:35]2[CH:40]=[CH:39][C:38]([F:41])=[C:37]([F:42])[CH:36]=2)[C:27]([CH2:26][NH:25][C:17](=[O:19])[C:16]2[CH:20]=[CH:21][C:22]([CH3:24])=[N:23][C:15]=2[Cl:14])=[N:31][N:30]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1217242-Chloro-6-methylnicotinic acidHCID 160435CarbodiimideHCID 178510680HCID 178510680, compound

Product 1

HCID 178425854N-[[5-amino-4-[(3,4-difluorophenyl)hydrazinylidene]pyrazol-3-yl]methyl]-2-chloro-6-methylpyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a 10 mL reaction vessel containing PS-carbodiimide (2 eq, 175 mg) and HOBt (1.7 eq, 20 mg) was added a solution of 2-chloro-6-methylnicotinic acid (1.5 eq, 0.12 mmol) in anhydrous CH2Cl2 (2 mL) and anhydrous DMF (0.2 mL). The reaction mixture was stirred at ambient temperature under argon for 30 minutes before a solution of 5-aminomethyl-4-[(3,4-difluorophenyl)hydrazono]-4H-pyrazol-3-ylamine (20 mg, 0.079 mmol) in anhydrous DCM (3 mL) and anhydrous DMF (0.7 mL) was added. The reaction mixture was further stirred for approximately 16 hours before it was filtered, washed with DCM (3×3 mL) and concentrated under reduced pressure. The title compound was obtained as a yellow powder (yield 26%). MS (m/z, ES+): 406 (Cl35M+1, 20%), 408 (Cl37M+1, 10%).

Workup

  1. customTo a 10 mL reaction vessel
  2. additionwas added
  3. filtrationwas filtered
  4. washwashed with DCM (3×3 mL)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b45811cee9b54b5a91bf9973532b403a
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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